As the camera zooms in on Christina Walters, a 28-year-old interior designer with a reputation for being a formidable force in San Francisco's vibrant singles scene, a chorus of voices spills forth. Her friends describe her as a master manipulator, gliding effortlessly through the social currents of the city, leaving a trail of heartaches and bruised egos in her wake.
Her close companion, Courtney Rockcliffe, a perceptive divorce lawyer, closely understands Christina’s character. Together, they decide to lift the spirits of their mutual friend Jane, who has just ended a relationship, by treating her to an exciting night at a well-known dance club in North Beach. As the night unfolds, Christina aims to play matchmaker, introducing Jane to Peter, a captivating stranger. However, when Peter turns out to be an outspoken critic of Christina's dubious romantic strategies, he walks away from her mid-conversation, leaving her feeling embarrassed and defeated.
While in the ladies' room during a heart-to-heart with Courtney, Christina reveals a surprising vulnerability, hinting that Peter might have unintentionally broken through her tough exterior, awakening emotions she thought were long buried. Despite her strong denials of any romantic feelings, her friends remain unconvinced.
The next evening, Christina unexpectedly runs into Peter again at the same club. As they share drinks, he mentions his plans to attend his brother Roger's wedding on Saturday, accompanied by a group of beautiful women. He invites both Christina and Courtney to the after-party at their hotel suite, yet Christina ultimately passes on the opportunity, a decision she soon regrets.
The following day, during a leisurely luncheon with Courtney, the conversation revolves around Peter. Meanwhile, Jane has an embarrassing brush with her ex-boyfriend at the dry cleaner's. In a moment of spontaneity, Courtney books flights for herself and Christina to Somerset, where Peter's brother is set to wed, allowing them to reunite with Jane's former flame at the ceremony.
As they drive off in Courtney's dependable Saab 9-5, the trio embarks on a series of wild escapades, which include an exploding toilet, the shocking discovery of a hidden glory hole, and a misunderstanding with a motorcyclist who mistakenly believes Courtney is involved in a shocking act with Christina while driving.
Amidst Jane's secret rendezvous with her boyfriend unfold in a retail store's changing room, Christina and Courtney find themselves in Somerset, soaked and disheveled from the relentless rain. Seeking fresh clothes, they stumble into a store only to come out dressed in garish and ill-fitting outfits.
Upon arrival at the wedding, Christina’s uncertainties fade as they undergo a series of coincidental events, leading to a fortuitous meeting with the bride, which encourages her to attend the ceremony. Their participation is cut short when they realize that Peter is, in fact, the groom, not Roger. In a frantic rush to escape, they nearly cause a scene at the wedding.
Ultimately, the wedding is canceled, prompting Christina and Courtney to return home, where they play pivotal roles in helping Jane escape an awkward situation with her boyfriend, who inadvertently calls for emergency services. Fast forward several months, and Christina finds herself yearning for love once again, while Courtney appears to have found joy with her doctor partner.
Meanwhile, driven by a quest for self-understanding, Peter seeks out Christina’s whereabouts through a logbook from their previous shopping adventure. Determined to face his fears and embrace love, he professes his enduring affection for Christina, only to be met with rejection. Undeterred, Peter shares his story in an interview, portraying Christina as a ruthless player who has left him wounded and rejected.
In an unexpected twist, Peter reveals that despite their rocky history, he and Christina have eventually found common ground, exchanging vows and weaving a life together with Jane, Courtney, and Roger, who has now achieved his own happiness in life.
